Starting with a minor role on Forever Fernwood in 1977, Penny has appeared in numerous TV films and television series, including in major roles on Riptide and Jake and the Fatman. He has also made many guest appearances on television shows including Touched by an Angel, T. J. Hooker, Vega$, Matt Houston, Lou Grant, CHiPs, Flamingo Road, The Sopranos, Diagnosis: Murder, Walker, Texas Ranger, Archie Bunker's Place, 7th Heaven, Tucker's Witch, Boomtown, The Gangster Chronicles, and CSI. In 2005, he co-starred with Lea Thompson in the mystery series Jane Doe on the Hallmark Channel.